1956 Harley-Davidson 165

A revolution in off-roading

When you think of lightweight off-road motorcycles, you probably don’t think of Harley-Davidson. But there was a time in the late ’50s when, thanks to the ingenuity of rider Leroy Winters, Harley was on the cutting edge of the lightweight off-road movement.

Back then, Michigan’s grueling, two-day, 500-mile Jack Pine Enduro was the biggest off-road event of the year. And from 1923 through 1955, riders on Harley-Davidsons won 22 of 28 Jack Pines.

All of those wins, though, came on heavyweight bikes designed for road use and only slightly modified for rough terrain. Conventional wisdom held that you needed lots of power, wide tires and lots of weight on the rear wheel to win in the deep sugar sand of Michigan.

But Winters had a different idea. He began with a diminutive two-stroke machine that carried the Harley name even though it was designed by the German DKW firm. In the peace talks following World War II, the rights to the highly regarded DKW 125 were awarded to both Harley and BSA as part of Germany’s war reparations. The BSA version of the machine became the Bantam, while the Harley version began life as the 125, then was enlarged to become the 165.

Winters took a light, agile 165, modified it for the dirt, and rode it to victory in the 1956 Jack Pine, beating machines with four or even six times that displacement, and surviving a course that eliminated three-quarters of the entrants.

It would take another decade before the two-stroke, lightweight movement would really catch on in off-road riding circles, and by that time, the movement was led by European manufacturers. But here in the U.S., enduro fans got a glimpse of the future during the 1956 Jack Pine in the form of a motorcycle bearing the Harley-Davidson name.

Winters’ winning bike, complete with the swingarm rear suspension and modified fuel tank he added for off-road competition, is currently on display in the Motorcycle Hall of Fame Museum at AMA headquarters in Pickerington, Ohio.